Sodium borohydride → tert-butyl {2-[3-{[(5-chloro-1H-indol-2-yl)carbonyl]amino}-2-oxo-3,4-dihydroquinolin-1 (2H)-yl]ethyl}carbamate

HRID 1376160Notes

Reaction equation

HRID 1376160 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([O:10]C([O-])=O)=O)([CH3:6])([CH3:5])[CH3:4].[Cl:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19]([C:24]([NH:26][CH:27]1[CH2:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]([CH2:37][C:38]#[N:39])[C:28]1=[O:40])=[O:25])=[CH:18]2>CO.C1COCC1.O.O.O.O.O.O.[Co](Cl)Cl>[Cl:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][C:19]([C:24]([NH:26][CH:27]1[CH2:36][C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:29]([CH2:37][CH2:38][NH:39][C:8](=[O:10])[O:7][C:3]([CH3:4])([CH3:5])[CH3:6])[C:28]1=[O:40])=[O:25])=[CH:18]2

Participants

7

Reactant 3

HCID 4311764Sodium borohydrideHCID 100452425-chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamideHCID 22064466Tert-butyldicarbonate

Product 1

HCID 58788457tert-butyl {2-[3-{[(5-chloro-1H-indol-2-yl)carbonyl]amino}-2-oxo-3,4-dihydroquinolin-1 (2H)-yl]ethyl}carbamateYield 94.2%

Reagents, catalysts & solvents 3

HCID 517166Dichlorocobalt hexahydrateCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared using an identical procedure as for Example 44 with sodium borohydride (1298 mg, 34.3 mmol), cobalt chloride hexahydrate (1632 mg, 6.86 mmol), tert-butyldicarbonate (1497 mg, 6.86 mmol) and 5-chloro-N-[1-(cyanomethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-1H-indole-2-carboxamide (Method 11, 1299 mg, 3.43 mmol) in MeOH (15 mL) and THF (10 mL). The reaction was stirred at ambient temperature for 1.5 h to give the title compound (1560 mg, 94%) as a pale tan solid.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-ba88095173a1449588d7ee0d936af374
Source dataset
uspto-grants-2007_01
Patent number
US07169927B2

Reaction notes

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